1-[1-(3-hydroxyphenyl)ethyl]piperidine | 124476-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-[1-(3-hydroxyphenyl)ethyl]piperidine
• 英文别名: 3-[1-(piperidin-1-yl)ethyl]phenol；3-[1-(1-Piperidinyl)ethyl]phenol；3-(1-Piperidin-1-ylethyl)phenol
• CAS: 124476-34-2
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: UMPJNZRSCUYXPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,N-二乙基氯甲酰胺 、 1-[1-(3-hydroxyphenyl)ethyl]piperidine 在 吡啶 、 三乙胺 作用下， 以68%的产率得到1-[1-(3-diethylcarbamoyloxyphenyl)ethyl]piperidine
  参考文献：
  名称：

  Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease

  摘要：

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01324-1
• 作为产物：
  描述：

  1-(1-氯乙基)-3-甲氧基苯 在 氢溴酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 1-[1-(3-hydroxyphenyl)ethyl]piperidine
  参考文献：
  名称：

  Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease

  摘要：

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01324-1

文献信息

• High-Throughput Screening of Reductive Amination Reactions Using Desorption Electrospray Ionization Mass Spectrometry
  作者：David L. Logsdon、Yangjie Li、Tiago Jose Paschoal Sobreira、Christina R. Ferreira、David H. Thompson、R. Graham Cooks

  DOI：10.1021/acs.oprd.0c00230

  日期：2020.9.18

  screening system that is capable of screening thousands of organic reactions in a single day. This system combines a liquid handling robot with desorption electrospray ionization (DESI) mass spectrometry (MS) for a rapid reaction mixture preparation, accelerated synthesis, and automated MS analysis. A total of 3840 unique reductive amination reactions were screened to demonstrate the throughputs that are

  这项研究描述了最新一代的高通量筛选系统，该系统能够在一天内筛选成千上万的有机反应。该系统将液体处理机器人与解吸电喷雾电离（DESI）质谱（MS）相结合，可快速制备反应混合物，加快合成速度并自动进行MS分析。总共筛选了3840个独特的还原胺化反应，以证明该系统具备的通量。产物，副产物和中间体均在全扫描质谱图中进行监控，从而生成反应进程的完整视图。进行串联质谱实验以验证所形成产物的身份。数据中显示的胺和亲电子反应性趋势符合理论预期，表示系统可以准确地对反应性能进行建模。DESI结果与使用更传统的质谱技术（例如液相色谱-质谱）生成的数据相关性很好，从而验证了系统生成的数据。
• Phenoxypropyl amine derivatives, process for their preparation, and pharmaceutical compositions containing them
  申请人：TEIKOKU HORMONE MFG. CO., LTD.

  公开号：EP0024510B1

  公开（公告）日：1983-10-19
• US4293557A
  申请人：——

  公开号：US4293557A

  公开（公告）日：1981-10-06
• Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease
  作者：C MUSTAZZA、A BORIONI、M GIUDICE、F GATTA、R FERRETTI、A MENEGUZ、M VOLPE、P LORENZINI

  DOI：10.1016/s0223-5234(01)01324-1

  日期：2002.2

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Design, synthesis, and evaluation of 2-phenoxy-indan-1-one derivatives as acetylcholinesterase inhibitors
  作者：Rong Sheng、Xiao Lin、Jingya Li、Yanke Jiang、Zhicai Shang、Yongzhou Hu

  DOI：10.1016/j.bmcl.2005.05.132

  日期：2005.9

  A series of 2-phenoxy-indan-1-one derivatives have been designed, synthesized, and tested as acetylcholinesterase inhibitors. The most potent compound exhibited high AChE inhibitory activity (IC50 = 50 nM), and the molecular docking study indicated that it was nicely accommodated by AChE. (c) 2005 Elsevier Ltd. All rights reserved.